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Sodium hydride → HCID 117992948, Verbindung

HRID 587982
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 587982
[CH3:1][O:2][C:3](=[O:15])[CH:4](P(OCC)(OCC)=O)[CH2:5][CH3:6].[H-].[Na+].[C:18]([O:22][C:23]([C:25]1[S:26][C:27]([CH:30]=O)=[CH:28][CH:29]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>O1CCCC1>[C:18]([O:22][C:23]([C:25]1[S:26][C:27](/[CH:30]=[C:4](/[C:3]([O:2][CH3:1])=[O:15])\[CH2:5][CH3:6])=[CH:28][CH:29]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 12565589HCID 12565589, VerbindungHCID 21473735Tert-butyl 5-formylthiophene-2-carboxylate

Produkt 1

HCID 117992948HCID 117992948, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-(Diethylphosphono)butyric acid methyl ester (46 g, 0.193 mol) was dissolved in tetrahydrofuran (300 mL), 60% sodium hydride (6.6 g, 0.165 mol) was added at 0° C., and the mixture was stirred for 30 minutes. To the reaction mixture was added a solution of 5-formyl-2-thiophenecarboxylic acid tert-butyl ester obtained in Example 1, step 2 (32.1 g, 0.15 mol) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated, and the residue was partitioned between ethyl acetate and 1N-hydrochloric acid solution, and washed successively with water and brine. After drying over anhydrous magnesium sulfate, the residue was purified by silica gel column chromatography to give the title compound (35.6 g, 0.12 mol, 80%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between ethyl acetate and 1N-hydrochloric acid solution
  4. washwashed successively with water and brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8aba03b041b94af79bf8b3335607fbd1
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09227949B2

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